This paper explores how strategic management concepts, especially the notion of 'wicked problems', can be useful in analysing the professional practice of teachers in higher education. The keeping of a dialogical journal with a colleague helped illuminate that strategic management and education have much in common. Both are situated in unstable, unpredictable environments where contradictory demands and conditions exist. The keeping of the journal points to some of the difficulties in self-reflection illustrating the need for a more refined understanding and definition of reflective practice in education. The paper does not attempt to promote an agenda for efficient teaching, or suggests what teachers should do. However, clearly distinguishing between educational problems and technical or managerial problems will serve the educational interests of teachers, students and institutions.